the windy city tour
The Windy City Tour
*Customize and personalize The Windy City Tour itinerary with our team
Sample: The Windy City Tour Itinerary
Day 1: Arrival & Group Dinner
- Travel to Chicago
- Arrival in Chicago and Meet Landmark Leader
- Group sit-down dinner
- Check-in to hotel accommodations
Day 2: Navy Pier & Skydeck Chicago at Willis Tower
- Hotel Breakfast
- Architecture River Cruise
- Lunch at Navy Pier and Group Exploration
- Group sit-down dinner
- Visit the Skydeck Chicago at Willis Tower
- Return to hotel accommodations
Day 3: Shedd Aquarium & Cubs Game at Wrigley Field
- Hotel Breakfast
- Visit the Shedd Aquarium
- Lunch at the museum
- Return to Hotel
- Dinner at Wrigley Field
- Attend a Chicago Cubs game at Wrigley Field
- Boxed sandwich lunch
- Return to hotel accommodations
Day 4: Art Institute of Chicago Museum & Magnificent Mile
- Hotel Breakfast
- Guided Walking Tour– Buckingham Fountain, Millennium Park, and the Cloud Gate
- Visit the Art Institute of Chicago Museum
- Lunch: City Cruise Experience on Lake Michigan
- Explore the Magnificent Mile
- Group sit-down dinner
- Visit 360 Chicago + Tilt Admission
- Return to hotel accommodations
Day 5: Departure
- Hotel Breakfast
- Depart for Home
Explore the Windy City Tour Itinerary
Embark on an exciting five-day educational adventure in Chicago, designed to captivate students of all grade levels! Discover the rich history, iconic landmarks, and cultural treasures of the Windy City with visits to Millennium Park, the Willis Tower, and Navy Pier. From exploring world-class museums and taking a scenic architecture boat tour to experiencing the vibrant culture and history of Chicago, this trip promises an immersive, hands-on learning experience that will leave students inspired and excited about art, science, and urban innovation.
Why Choose a Chicago Educational Tour?
Iconic Landmarks: Explore famous sites like Millennium Park, the Willis Tower, Navy Pier, and the historic Chicago Riverwalk for a deeper connection to the city’s rich culture.
World-Class Museums: Discover hands-on learning opportunities at institutions like the Field Museum, the Art Institute of Chicago, and the Museum of Science and Industry.
Architecture and Innovation: Experience Chicago’s legendary architecture with guided tours, including a scenic riverboat cruise showcasing the city’s skyline and engineering marvels.
Cultural Diversity: Immerse students in the vibrant cultural tapestry of Chicago, exploring neighborhoods like Chinatown, Little Italy, and Pilsen.
Note: This is a SAMPLE itinerary provided for inspiration only. (Unless you love it!) Every trip we offer is fully customizable, ensuring a personalized experience tailored to your school’s educational goals.
Trip Inclusions – Tailored Just for You
Work with our expert Destination Landmark Specialist team to design a trip that fits your group’s unique needs!
Our packages start fully customizable and typically include:
- Private Group Tour – Personalized experiences for your group only.
- Custom Itinerary – Built around your educational goals and preferences.
- Transportation – Safe, reliable, and comfortable travel.
- Hotel Accommodations – Convenient and student-friendly lodging.
- Attractions – Access to top-rated sites and experiences.
- Meals – Delicious and well-balanced dining options.
- Tour Manager – Professional support throughout your journey.
- Restaurant & Driver Gratuities – Taken care of for your convenience.
- & More!
You have the flexibility to include or exclude specific services based on your group’s preferences. While we recommend the value of an all-inclusive travel experience, the final decision is yours! Let us create your next seamless and unforgettable group adventure!

- 5 Days / 4 Nights
- Chicago
TRAVEL TIPS
Tip: Book Early!
Booking early secures the best rates, preferred accommodations, and prime access to popular attractions. It also allows more time for trip planning, ensuring a smooth and stress-free travel experience.
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Discover customizable Chicago travel packages designed for educational tours, student groups, and more!